The majority of early education programs promote children's learning through a mix of experiences in child- and teacher-managed contexts. The current study examined time spent in child- and teacher-managed contexts and the nature of children's experiences with teachers in these contexts as they relate to children's skill development. Participants were preschool children (N = 283, M age = 52 months, 48% girls, 70% Mexican or Mexican American) from families of a lower socioeconomic status. Observations captured children's time in child- and teacher-managed contexts and experiences with teachers in each context. School readiness was assessed directly and through teacher reports. Research Findings: Time spent in teacher-managed contexts was positively related to children's academic and social skill development. Experiences in child-managed context predicted vocabulary, math, and social skills when teachers were directly involved with children. Overall, the findings suggest that teacher engagement is related to positive outcomes even during child-managed activities. Practice or Policy: Given these findings, preservice and professional development programs for early childhood educators should have a component that focuses on how to enhance the teacher's role during child-managed activities.